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Reactivity,Regioselectivity,and Synthetic Application of 2-Pyrenyl Units in Scholl Reactions

查看全文 作　　者：Sai Ho [1,2]Pun;Ethan Chi Ho [3]Wen;Zeming [1]Xia;Han [1]Chen;Felix [3,4,5,6]RFischer;Qian [1]Miao 高影响力作者 机构地区：[1]Department of Chemistry,The Chinese University of Hong Kong,Hong Kong;[2]Department of Chemistry,University of Cologne,Cologne;[3]Department of Chemistry,University of California,Berkeley,California 94720;[4]Materials Sciences Division,Lawrence Berkeley National Laboratory,Berkeley,California 94720;[5]Kavli Energy NanoScience Institute at the University of California Berkeley and the Lawrence Berkeley National Laboratory,Berkeley,California 94720;[6]Bakar Institute of Digital Materials for the Planet,Division of Computing,Data Science,and Society,University of California,Berkeley,California 94720高影响力机构 出　　处：《CCS Chemistry》索引2023年第5卷第9期,共9页高影响力期刊 基　　金：supported by the University Grants Committee(Hong Kong)through a Research Matching Grant,Deutsche Forschungsgemeinschaft(DFG)through the research training group“Template-Designed Organic Electronics(TIDE)”(RTG 2591);the U.S.Department of Energy(DOE),Office of Science,Basic Energy Sciences(BES),Materials Sciences and Engineering Division under contract no.DE-AC02-05-CH11231(Nanomachine program KC1203)and contract no.DE-SC0023105. 摘　　要：We herein report the reactivity and regioselectivity of 2-pyrenyl as a coupling unit in Scholl reactions.On the basis of the Scholl reactions of hexaarylbenzene substrates,we have found that pyrenyl units are preferably oxidized over naphthyl and phenyl units under appropriate Scholl reaction conditions,allowing divergent synthesis through a highly controllable intramolecular coupling sequence.We find that the C1 and C3 positions of the 2-pyrenyl unit are the favorable sites for intramolecular coupling while C4 is not reactive to allow further coupling.The reactivity and regioselectivity pattern can be explained by the spin density distribution,which shows that carbon-carbon bonds preferably form at sites with higher positive spin density.Guided by these findings,we successfully synthesized a double helicene and a sextuple helicene through the controlled Scholl reactions of 2-pyrenyl units. 关 键 词：HELICENE polycyclic aromatics PYRENE Scholl reactions spin density
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